title: Long-chain ethers as solvents can amplify the enantioselectivity of the Carica papaya lipase-catalyzed transesterification of 2-(substituted phenoxy)propanoic acid esters.
abstract: The enantioselectivity of the transesterification of the 2,2,2-trifluoroethyl esters of 2-(substituted phenoxy)propanoic acids, as catalyzed by the lipase from Carica papaya, was greatly improved by using long-chain ethers, such as di-n-hexyl ether, as solvents instead of the conventional diisopropyl ether. Thus, for example, the E value was enhanced from 21 [in diisopropyl ether (0.8 ml)] to 57 [in di-n-hexyl ether (0.8 ml)] in the reaction of 2,2,2-trifluoroethyl(RS)-2-phenoxypropanoate (0.1 mmol) with methanol (0.4 mmol) in the presence of the plant lipase preparation (10 mg); it was also improved from 13 (in diisopropyl ether) to 44 (in di-n-hexyl ether) in the reaction of 2,2,2-trifluoroethyl(RS)-2-(2-chlorophenoxy)propanoate with methanol under the same reaction conditions.
authors.affiliation: Department of Chemistry, Faculty of Science and Engineering, Konan University, Higashinada-ku, Kobe, 658-8501, Japan, miyazawa@konan-u.ac.jp.
authors.forename: Toshifumi
authors.initials: T
authors.lastname: Miyazawa
authors.forename: Wakana
authors.initials: W
authors.lastname: Iguchi
mesh_terms: D029441:Carica / Q000201:enzymology*; D004951:Esterification; D004952:Esters / Q000378:metabolism*; D004987:Ethers / Q000737:chemistry*; D008049:Lipase / Q000378:metabolism*; D011422:Propionates / Q000378:metabolism*; D012997:Solvents / Q000737:chemistry*; D013379:Substrate Specificity / Q000187:drug effects
chemical_list: D004952:Esters; D004987:Ethers; D011422:Propionates; D012997:Solvents; D008049:Lipase